Assuming the variable 'man is of Type MANAGED, and is assigned, this code will work:
MANAGED man = MANAGED.TYPE1;
UNMANAGED un = (UNMANAGED)((int)man);
An obvious bug is your use of the word 'class here:
enum class MANAGED.
This will work:
MANAGED man = MANAGED.TYPE1;
UNMANAGED un = (UNMANAGED) man;
Because each Enum value has an intrinsic numeric value: conversion (to integer) is not required.